1,2-Dichloroethane → 2-(Benzyloxy)-2-oxoethyl 4-(methylsulfonamido-methyl)benzoate

HRID 1776559노트

반응식

HRID 1776559 반응식
[CH3:1][S:2]([NH:5][CH2:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1)(=[O:4])=[O:3].O[CH2:17][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19].C(Cl)CCl>C(Cl)Cl.C(Cl)Cl.CO.CN(C1C=CN=CC=1)C>[CH3:1][S:2]([NH:5][CH2:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([O:13][CH2:17][C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])=[O:12])=[CH:9][CH:8]=1)(=[O:4])=[O:3]

참가 물질

7

반응물 3

HCID 111,2-DichloroethaneHCID 561337Benzyl 2-hydroxyacetateHCID 15066094-{[(Methylsulfonyl)amino]methyl}benzoic acid

생성물 1

HCID 866795152-(Benzyloxy)-2-oxoethyl 4-(methylsulfonamido-methyl)benzoate수율 60.7%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매HCID 21226129Dichloromethane methanol용매

실험 절차

To a solution of 4-(methylsulfonamidomethyl)benzoic acid (0.4 g, 1.745 mmol) and benzyl 2-hydroxyacetate (0.290 g, 1.745 mmol) in a mixture of DCM and THF 1/1 (50 ml), EDC (0.334 g, 1.745 mmol) and DMAP (0.256 g, 2.094 mmol) were added in one portion. The reaction was stirred at RT for 3 hours. The solvent was removed under vacuum and the resulting crude was portioned between EtOAc and HCl 2N. The organic phase was separated, washed with brine and dried over Na2SO4. The solvent was removed under vacuum affording 2-(benzyloxy)-2-oxoethyl 4-(methylsulfonamido-methyl)benzoate (0.4 g, 1.060 mmol, 60.7% yield, MS/ESI+ 377.9 [MH]+). This product was employed in the following step without any further purification.

후처리

  1. additionwere added in one portion
  2. customThe solvent was removed under vacuum
  3. customThe organic phase was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed under vacuum

출처 및 근거

ORD 기록
ord-ac348c8047d345f4a89be2d61033404a
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09265768B2

반응 노트

불러오는 중…